CA1156655A - 2-amino-3-[hydroxy(phenyl)methyl] phenylacetic acids, esters and amides - Google Patents
2-amino-3-[hydroxy(phenyl)methyl] phenylacetic acids, esters and amidesInfo
- Publication number
- CA1156655A CA1156655A CA000371185A CA371185A CA1156655A CA 1156655 A CA1156655 A CA 1156655A CA 000371185 A CA000371185 A CA 000371185A CA 371185 A CA371185 A CA 371185A CA 1156655 A CA1156655 A CA 1156655A
- Authority
- CA
- Canada
- Prior art keywords
- amino
- compound
- loweralkyl
- process according
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- SULMNCIGVRMBIU-UHFFFAOYSA-N 2-[2-amino-3-[hydroxy(phenyl)methyl]phenyl]acetic acid Chemical class NC1=C(CC(O)=O)C=CC=C1C(O)C1=CC=CC=C1 SULMNCIGVRMBIU-UHFFFAOYSA-N 0.000 title claims abstract 3
- 150000001408 amides Chemical class 0.000 title abstract description 9
- 150000002148 esters Chemical class 0.000 title abstract description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 52
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 26
- 239000001257 hydrogen Substances 0.000 claims abstract description 26
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 17
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 13
- 150000002367 halogens Chemical class 0.000 claims abstract description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 12
- 150000001768 cations Chemical class 0.000 claims abstract description 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 10
- 150000004677 hydrates Chemical class 0.000 claims abstract description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims abstract description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 33
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 27
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 25
- 239000011734 sodium Substances 0.000 claims description 19
- -1 morpholino, pyrrolidino, piperidino Chemical group 0.000 claims description 15
- 229910052708 sodium Inorganic materials 0.000 claims description 14
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 13
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 13
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 12
- 239000012279 sodium borohydride Substances 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 11
- 239000000460 chlorine Substances 0.000 claims description 7
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 238000005984 hydrogenation reaction Methods 0.000 claims description 5
- 229910052727 yttrium Inorganic materials 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 230000020477 pH reduction Effects 0.000 claims description 3
- MJAQSCHBMPGJES-UHFFFAOYSA-M sodium (2-amino-3-benzoylphenyl)acetate Chemical compound [Na+].NC1=C(CC([O-])=O)C=CC=C1C(=O)C1=CC=CC=C1 MJAQSCHBMPGJES-UHFFFAOYSA-M 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 7
- 238000004519 manufacturing process Methods 0.000 claims 6
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims 3
- 238000006386 neutralization reaction Methods 0.000 claims 3
- VUMFVUKYSQDAJD-UHFFFAOYSA-N 2-[2-amino-3-[(4-chlorophenyl)-hydroxymethyl]phenyl]acetic acid Chemical compound NC1=C(CC(O)=O)C=CC=C1C(O)C1=CC=C(Cl)C=C1 VUMFVUKYSQDAJD-UHFFFAOYSA-N 0.000 claims 2
- AAAYAHLNKYKTKK-UHFFFAOYSA-N 2-[2-amino-5-chloro-3-[hydroxy(phenyl)methyl]phenyl]acetic acid Chemical compound NC1=C(C=C(C=C1C(C1=CC=CC=C1)O)Cl)CC(=O)O AAAYAHLNKYKTKK-UHFFFAOYSA-N 0.000 claims 2
- CRZQGDNQQAALAY-UHFFFAOYSA-N Methyl benzeneacetate Chemical compound COC(=O)CC1=CC=CC=C1 CRZQGDNQQAALAY-UHFFFAOYSA-N 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- FVBKCOXGVZPEDP-UHFFFAOYSA-M sodium;2-[2-amino-3-(4-chlorobenzoyl)phenyl]acetate Chemical compound [Na+].NC1=C(CC([O-])=O)C=CC=C1C(=O)C1=CC=C(Cl)C=C1 FVBKCOXGVZPEDP-UHFFFAOYSA-M 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 1
- SWAULJUBWSQJIE-UHFFFAOYSA-M sodium;2-(2-amino-3-benzoyl-5-chlorophenyl)acetate Chemical compound [Na+].NC1=C(CC([O-])=O)C=C(Cl)C=C1C(=O)C1=CC=CC=C1 SWAULJUBWSQJIE-UHFFFAOYSA-M 0.000 claims 1
- QFCJIDHMYDIPOP-UHFFFAOYSA-M sodium;2-[2-amino-3-[(4-chlorophenyl)-hydroxymethyl]phenyl]acetate Chemical compound [Na+].NC1=C(CC([O-])=O)C=CC=C1C(O)C1=CC=C(Cl)C=C1 QFCJIDHMYDIPOP-UHFFFAOYSA-M 0.000 claims 1
- QEXUQZXGARIKTK-UHFFFAOYSA-M sodium;2-[2-amino-3-[hydroxy(phenyl)methyl]phenyl]acetate Chemical compound [Na+].NC1=C(CC([O-])=O)C=CC=C1C(O)C1=CC=CC=C1 QEXUQZXGARIKTK-UHFFFAOYSA-M 0.000 claims 1
- 150000003839 salts Chemical class 0.000 abstract description 10
- 239000002184 metal Chemical class 0.000 abstract description 6
- 229910052751 metal Inorganic materials 0.000 abstract description 6
- 230000003110 anti-inflammatory effect Effects 0.000 abstract description 4
- 230000001760 anti-analgesic effect Effects 0.000 abstract description 2
- 230000001754 anti-pyretic effect Effects 0.000 abstract description 2
- 239000002221 antipyretic Substances 0.000 abstract description 2
- 230000002401 inhibitory effect Effects 0.000 abstract description 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 abstract description 2
- 208000010110 spontaneous platelet aggregation Diseases 0.000 abstract description 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 78
- 239000000243 solution Substances 0.000 description 69
- LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical compound NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 description 59
- 239000000203 mixture Substances 0.000 description 46
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
- 238000002360 preparation method Methods 0.000 description 29
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
- 238000004458 analytical method Methods 0.000 description 28
- 229940073584 methylene chloride Drugs 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 19
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 17
- 239000007787 solid Substances 0.000 description 17
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 14
- 239000004480 active ingredient Substances 0.000 description 14
- 239000000706 filtrate Substances 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- 229910014033 C-OH Inorganic materials 0.000 description 12
- 229910014570 C—OH Inorganic materials 0.000 description 12
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 12
- IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 0.000 description 10
- 229940086542 triethylamine Drugs 0.000 description 10
- 239000007868 Raney catalyst Substances 0.000 description 9
- 229910000564 Raney nickel Inorganic materials 0.000 description 9
- 235000019441 ethanol Nutrition 0.000 description 8
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 8
- 235000019341 magnesium sulphate Nutrition 0.000 description 8
- 241001465754 Metazoa Species 0.000 description 7
- IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 description 7
- 229940049953 phenylacetate Drugs 0.000 description 7
- MAOBFOXLCJIFLV-UHFFFAOYSA-N (2-aminophenyl)-phenylmethanone Chemical compound NC1=CC=CC=C1C(=O)C1=CC=CC=C1 MAOBFOXLCJIFLV-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 6
- 239000002775 capsule Substances 0.000 description 6
- 239000008101 lactose Substances 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- ZUWXHHBROGLWNH-UHFFFAOYSA-N (2-amino-5-chlorophenyl)-phenylmethanone Chemical compound NC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 ZUWXHHBROGLWNH-UHFFFAOYSA-N 0.000 description 5
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 5
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 229920002472 Starch Polymers 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 229960003424 phenylacetic acid Drugs 0.000 description 4
- 239000003279 phenylacetic acid Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- KJRCEJOSASVSRA-UHFFFAOYSA-N propane-2-thiol Chemical compound CC(C)S KJRCEJOSASVSRA-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000008107 starch Substances 0.000 description 4
- 235000019698 starch Nutrition 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 229960004132 diethyl ether Drugs 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000003937 drug carrier Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- QEFAQIPZVLVERP-UHFFFAOYSA-N nepafenac Chemical compound NC(=O)CC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1N QEFAQIPZVLVERP-UHFFFAOYSA-N 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- XJDQUPFWVIUWNZ-UHFFFAOYSA-N o-ethyl propanethioate Chemical compound CCOC(=S)CC XJDQUPFWVIUWNZ-UHFFFAOYSA-N 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000008174 sterile solution Substances 0.000 description 3
- BNUTYMOAQFOMEB-UHFFFAOYSA-N 2-(2-amino-3-benzoyl-5-chlorophenyl)acetamide Chemical compound NC(=O)CC1=CC(Cl)=CC(C(=O)C=2C=CC=CC=2)=C1N BNUTYMOAQFOMEB-UHFFFAOYSA-N 0.000 description 2
- QDJLJVRESHRIBY-UHFFFAOYSA-N 2-[2-amino-3-(2-fluorobenzoyl)phenyl]acetamide Chemical compound NC(=O)CC1=CC=CC(C(=O)C=2C(=CC=CC=2)F)=C1N QDJLJVRESHRIBY-UHFFFAOYSA-N 0.000 description 2
- LPYKIKWWPFNVKP-UHFFFAOYSA-N 2-[2-amino-3-[4-(trifluoromethyl)benzoyl]phenyl]acetamide Chemical compound NC(=O)CC1=CC=CC(C(=O)C=2C=CC(=CC=2)C(F)(F)F)=C1N LPYKIKWWPFNVKP-UHFFFAOYSA-N 0.000 description 2
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 2
- WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 description 2
- CJXBHFANXQMZBF-UHFFFAOYSA-N 2-phenylethanethioamide Chemical compound NC(=S)CC1=CC=CC=C1 CJXBHFANXQMZBF-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 229920002261 Corn starch Polymers 0.000 description 2
- 235000019739 Dicalciumphosphate Nutrition 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
- 210000001772 blood platelet Anatomy 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000001506 calcium phosphate Substances 0.000 description 2
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 2
- 235000013539 calcium stearate Nutrition 0.000 description 2
- 239000008116 calcium stearate Substances 0.000 description 2
- 239000008120 corn starch Substances 0.000 description 2
- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 2
- 229940038472 dicalcium phosphate Drugs 0.000 description 2
- 229910000390 dicalcium phosphate Inorganic materials 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 238000005187 foaming Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- OJEGAMHXVWSGDH-UHFFFAOYSA-N n-methyl-2-methylsulfanylacetamide Chemical compound CNC(=O)CSC OJEGAMHXVWSGDH-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- BJALDACDVYCCOM-UHFFFAOYSA-M sodium;2-[2-amino-3-(4-chlorobenzoyl)phenyl]acetate;hydrate Chemical compound O.[Na+].NC1=C(CC([O-])=O)C=CC=C1C(=O)C1=CC=C(Cl)C=C1 BJALDACDVYCCOM-UHFFFAOYSA-M 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- LFMHZYLLULKEAM-UHFFFAOYSA-N (2-aminophenyl)-(2,4-difluorophenyl)methanone Chemical compound NC1=CC=CC=C1C(=O)C1=CC=C(F)C=C1F LFMHZYLLULKEAM-UHFFFAOYSA-N 0.000 description 1
- NRAJMXHXQHCBHO-UHFFFAOYSA-N (2-aminophenyl)-(2-fluorophenyl)methanone Chemical compound NC1=CC=CC=C1C(=O)C1=CC=CC=C1F NRAJMXHXQHCBHO-UHFFFAOYSA-N 0.000 description 1
- APHLSUBLNQBFTM-UHFFFAOYSA-N (2-aminophenyl)-(4-chlorophenyl)methanone Chemical compound NC1=CC=CC=C1C(=O)C1=CC=C(Cl)C=C1 APHLSUBLNQBFTM-UHFFFAOYSA-N 0.000 description 1
- FFFXIQFESQNINT-UHFFFAOYSA-N (2-aminophenyl)-(4-fluorophenyl)methanone Chemical compound NC1=CC=CC=C1C(=O)C1=CC=C(F)C=C1 FFFXIQFESQNINT-UHFFFAOYSA-N 0.000 description 1
- KYWXRBNOYGGPIZ-UHFFFAOYSA-N 1-morpholin-4-ylethanone Chemical compound CC(=O)N1CCOCC1 KYWXRBNOYGGPIZ-UHFFFAOYSA-N 0.000 description 1
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 1
- QYWOBAQCODTFCM-UHFFFAOYSA-N 2-[2-amino-3-(4-chlorobenzoyl)phenyl]acetamide Chemical compound NC(=O)CC1=CC=CC(C(=O)C=2C=CC(Cl)=CC=2)=C1N QYWOBAQCODTFCM-UHFFFAOYSA-N 0.000 description 1
- GKMMHJDOPVEYMT-UHFFFAOYSA-N 2-[2-amino-3-[hydroxy(phenyl)methyl]-5-methoxyphenyl]acetic acid Chemical compound NC1=C(C=C(C=C1C(C1=CC=CC=C1)O)OC)CC(=O)O GKMMHJDOPVEYMT-UHFFFAOYSA-N 0.000 description 1
- KIYRSYYOVDHSPG-UHFFFAOYSA-N 2-amino-2-phenylacetamide Chemical class NC(=O)C(N)C1=CC=CC=C1 KIYRSYYOVDHSPG-UHFFFAOYSA-N 0.000 description 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 1
- NTMLLKRWCFUOAP-UHFFFAOYSA-N 3-oxo-2,3-diphenylpropanamide Chemical class C=1C=CC=CC=1C(C(=O)N)C(=O)C1=CC=CC=C1 NTMLLKRWCFUOAP-UHFFFAOYSA-N 0.000 description 1
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- COXVTLYNGOIATD-HVMBLDELSA-N CC1=C(C=CC(=C1)C1=CC(C)=C(C=C1)\N=N\C1=C(O)C2=C(N)C(=CC(=C2C=C1)S(O)(=O)=O)S(O)(=O)=O)\N=N\C1=CC=C2C(=CC(=C(N)C2=C1O)S(O)(=O)=O)S(O)(=O)=O Chemical compound CC1=C(C=CC(=C1)C1=CC(C)=C(C=C1)\N=N\C1=C(O)C2=C(N)C(=CC(=C2C=C1)S(O)(=O)=O)S(O)(=O)=O)\N=N\C1=CC=C2C(=CC(=C(N)C2=C1O)S(O)(=O)=O)S(O)(=O)=O COXVTLYNGOIATD-HVMBLDELSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- GXCLVBGFBYZDAG-UHFFFAOYSA-N N-[2-(1H-indol-3-yl)ethyl]-N-methylprop-2-en-1-amine Chemical compound CN(CCC1=CNC2=C1C=CC=C2)CC=C GXCLVBGFBYZDAG-UHFFFAOYSA-N 0.000 description 1
- QCIRHNQAOILPGE-UHFFFAOYSA-N N-[2-amino-3-[(4-fluorophenyl)-hydroxymethyl]phenyl]acetamide Chemical compound C(C)(=O)NC1=C(C(=CC=C1)C(C1=CC=C(C=C1)F)O)N QCIRHNQAOILPGE-UHFFFAOYSA-N 0.000 description 1
- SSEGXOGUAIJRJE-UHFFFAOYSA-N O.NC1=C(C=CC=C1C(C1=CC=CC=C1)O)CC(=O)O Chemical compound O.NC1=C(C=CC=C1C(C1=CC=CC=C1)O)CC(=O)O SSEGXOGUAIJRJE-UHFFFAOYSA-N 0.000 description 1
- 208000002151 Pleural effusion Diseases 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- BNPDAJSVJKSAGM-UHFFFAOYSA-N [3-(3,4-dichlorobenzoyl)phenyl] acetate Chemical compound CC(=O)OC1=CC=CC(C(=O)C=2C=C(Cl)C(Cl)=CC=2)=C1 BNPDAJSVJKSAGM-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- SOYCMDCMZDHQFP-UHFFFAOYSA-N amfenac Chemical class NC1=C(CC(O)=O)C=CC=C1C(=O)C1=CC=CC=C1 SOYCMDCMZDHQFP-UHFFFAOYSA-N 0.000 description 1
- QZNJPJDUBTYMRS-UHFFFAOYSA-M amfenac sodium hydrate Chemical compound O.[Na+].NC1=C(CC([O-])=O)C=CC=C1C(=O)C1=CC=CC=C1 QZNJPJDUBTYMRS-UHFFFAOYSA-M 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 229940069428 antacid Drugs 0.000 description 1
- 239000003159 antacid agent Substances 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 229940125716 antipyretic agent Drugs 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000007963 capsule composition Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000000679 carrageenan Substances 0.000 description 1
- 235000010418 carrageenan Nutrition 0.000 description 1
- 229920001525 carrageenan Polymers 0.000 description 1
- 229940113118 carrageenan Drugs 0.000 description 1
- VXIVSQZSERGHQP-UHFFFAOYSA-N chloroacetamide Chemical compound NC(=O)CCl VXIVSQZSERGHQP-UHFFFAOYSA-N 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 1
- XQGLNUVQVKZRRR-UHFFFAOYSA-N ethyl 2-(2-amino-3-benzoylphenyl)acetate Chemical compound CCOC(=O)CC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1N XQGLNUVQVKZRRR-UHFFFAOYSA-N 0.000 description 1
- FCZCIXQGZOUIDN-UHFFFAOYSA-N ethyl 2-diethoxyphosphinothioyloxyacetate Chemical compound CCOC(=O)COP(=S)(OCC)OCC FCZCIXQGZOUIDN-UHFFFAOYSA-N 0.000 description 1
- 229960003699 evans blue Drugs 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 235000001727 glucose Nutrition 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- XSIAJRFXWYEOJL-UHFFFAOYSA-N methyl 2-(2-amino-3-benzoylphenyl)acetate Chemical compound COC(=O)CC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1N XSIAJRFXWYEOJL-UHFFFAOYSA-N 0.000 description 1
- UDZFAFRZPOZZMR-UHFFFAOYSA-N methyl 2-[3-benzoyl-2-(dimethylamino)phenyl]acetate Chemical compound COC(=O)CC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1N(C)C UDZFAFRZPOZZMR-UHFFFAOYSA-N 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- LYDAHNXGYJRKLL-UHFFFAOYSA-N n,n-dimethyl-2-methylsulfanylacetamide Chemical compound CSCC(=O)N(C)C LYDAHNXGYJRKLL-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000013021 overheating Methods 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- FFXIGVUMVPUWDK-UHFFFAOYSA-N pentanethioamide Chemical compound CCCCC(N)=S FFXIGVUMVPUWDK-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- SMOPCACDYYHOPI-UHFFFAOYSA-M potassium;2-(2-amino-3-benzoylphenyl)acetate;hydrate Chemical compound O.[K+].NC1=C(CC([O-])=O)C=CC=C1C(=O)C1=CC=CC=C1 SMOPCACDYYHOPI-UHFFFAOYSA-M 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- WPZSAUFQHYFIPG-UHFFFAOYSA-N propanethioamide Chemical compound CCC(N)=S WPZSAUFQHYFIPG-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 1
- HHMNMLHPCDSULA-UHFFFAOYSA-M sodium;2-(2-amino-3-benzoylphenyl)acetate;dihydrate Chemical compound O.O.[Na+].NC1=C(CC([O-])=O)C=CC=C1C(=O)C1=CC=CC=C1 HHMNMLHPCDSULA-UHFFFAOYSA-M 0.000 description 1
- HJGDSOZCBAYTER-UHFFFAOYSA-M sodium;2-[2-amino-3-(4-methoxybenzoyl)phenyl]acetate Chemical compound [Na+].C1=CC(OC)=CC=C1C(=O)C1=CC=CC(CC([O-])=O)=C1N HJGDSOZCBAYTER-UHFFFAOYSA-M 0.000 description 1
- NASFKTWZWDYFER-UHFFFAOYSA-N sodium;hydrate Chemical compound O.[Na] NASFKTWZWDYFER-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
- 238000005550 wet granulation Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pain & Pain Management (AREA)
- Pharmacology & Pharmacy (AREA)
- Rheumatology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12254480A | 1980-02-19 | 1980-02-19 | |
| US122,544 | 1980-02-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1156655A true CA1156655A (en) | 1983-11-08 |
Family
ID=22403319
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000371185A Expired CA1156655A (en) | 1980-02-19 | 1981-02-18 | 2-amino-3-[hydroxy(phenyl)methyl] phenylacetic acids, esters and amides |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JPS56131552A (en, 2012) |
| AU (1) | AU538240B2 (en, 2012) |
| BE (1) | BE887566A (en, 2012) |
| CA (1) | CA1156655A (en, 2012) |
| CH (1) | CH648283A5 (en, 2012) |
| DE (1) | DE3105285A1 (en, 2012) |
| FR (1) | FR2476071A1 (en, 2012) |
| GB (1) | GB2071086B (en, 2012) |
| IL (1) | IL61945A (en, 2012) |
| IT (1) | IT1146744B (en, 2012) |
| NL (1) | NL8100808A (en, 2012) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA805476B (en) * | 1979-09-26 | 1981-11-25 | Robins Co Inc A H | 2-amino-3-benzoyl-phenylacetamides and cyclic homologues |
| IL64724A0 (en) * | 1981-02-17 | 1982-03-31 | Robins Co Inc A H | 2-amino-3-(halobenzoyl)-methylphenylacetic acids and esters and salts thereof and pharmaceutical compositions containing them |
| US5475034A (en) * | 1994-06-06 | 1995-12-12 | Alcon Laboratories, Inc. | Topically administrable compositions containing 3-benzoylphenylacetic acid derivatives for treatment of ophthalmic inflammatory disorders |
| AR030346A1 (es) | 2000-08-14 | 2003-08-20 | Alcon Inc | Metodo de tratamiento de desordenes neurodegenerativos de la retina y cabeza de nervio optico |
| AR030345A1 (es) * | 2000-08-14 | 2003-08-20 | Alcon Inc | Metodo de tratamiento de desordenes relacionados con angiogenesis |
| US6646003B2 (en) | 2001-04-02 | 2003-11-11 | Alcon, Inc. | Method of treating ocular inflammatory and angiogenesis-related disorders of the posterior segment of the eye using an amide derivative of flurbiprofen or ketorolac |
| TWI358290B (en) | 2004-12-02 | 2012-02-21 | Alcon Inc | Topical nepafenac formulations |
| CN102438979A (zh) * | 2009-03-12 | 2012-05-02 | 麦迪凯姆股份公司 | 苯甲酰基苯乙酰胺衍生物的新型晶体 |
| WO2010115906A1 (en) * | 2009-04-06 | 2010-10-14 | Medichem, S.A. | 2-{2-amino-3-[hydroxy(phenyl)methyl]phenyl} acetamide |
| CN106631881B (zh) * | 2016-09-08 | 2018-09-21 | 南京工业大学 | 2-（3-苄基-2-（二甲基氨基）苯基）乙酰胺及合成方法和用途 |
| CN112794809B (zh) * | 2019-11-14 | 2023-12-29 | 南京济群医药科技股份有限公司 | 一种高纯度奈帕芬胺中间体的制备方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE400966B (sv) * | 1975-08-13 | 1978-04-17 | Robins Co Inc A H | Forfarande for framstellning av 2-amino-3-(eller 5-)bensoyl-fenylettiksyror |
| FR2366015A1 (fr) * | 1975-11-05 | 1978-04-28 | Robins Co Inc A H | Nouveaux acides amino-2 benzoyl-3 (5 et 6) phenylacetiques et leurs esters et sels de metaux alcalins, utiles notamment comme anti-inflammatoires, et leur procede de preparation |
| ZA805476B (en) * | 1979-09-26 | 1981-11-25 | Robins Co Inc A H | 2-amino-3-benzoyl-phenylacetamides and cyclic homologues |
-
1981
- 1981-01-20 IL IL61945A patent/IL61945A/xx unknown
- 1981-02-09 IT IT67177/81A patent/IT1146744B/it active
- 1981-02-13 DE DE19813105285 patent/DE3105285A1/de not_active Withdrawn
- 1981-02-16 AU AU67330/81A patent/AU538240B2/en not_active Ceased
- 1981-02-18 GB GB8105091A patent/GB2071086B/en not_active Expired
- 1981-02-18 FR FR8103188A patent/FR2476071A1/fr active Granted
- 1981-02-18 CH CH1076/81A patent/CH648283A5/fr not_active IP Right Cessation
- 1981-02-18 CA CA000371185A patent/CA1156655A/en not_active Expired
- 1981-02-18 NL NL8100808A patent/NL8100808A/nl not_active Application Discontinuation
- 1981-02-18 BE BE0/203830A patent/BE887566A/fr not_active IP Right Cessation
- 1981-02-19 JP JP2363881A patent/JPS56131552A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| AU6733081A (en) | 1981-08-27 |
| IT1146744B (it) | 1986-11-19 |
| BE887566A (fr) | 1981-06-15 |
| FR2476071B1 (en, 2012) | 1984-05-11 |
| AU538240B2 (en) | 1984-08-02 |
| JPS56131552A (en) | 1981-10-15 |
| GB2071086A (en) | 1981-09-16 |
| FR2476071A1 (fr) | 1981-08-21 |
| DE3105285A1 (de) | 1982-01-21 |
| CH648283A5 (fr) | 1985-03-15 |
| GB2071086B (en) | 1984-02-08 |
| IT8167177A0 (it) | 1981-02-09 |
| JPH0153266B2 (en, 2012) | 1989-11-13 |
| IL61945A0 (en) | 1981-02-27 |
| IL61945A (en) | 1984-09-30 |
| NL8100808A (nl) | 1981-09-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4670566A (en) | 3-methyl-hio-4-(5-, 6-, or 7-)phenylindolindolin-2-ones | |
| US4440785A (en) | Methods of using 2-aminobiphenylacetic acids, esters, and metal salts thereof to treat inflammation | |
| US4313949A (en) | Method of producing an inhibitory effect on blood platelet aggregation | |
| NO170883B (no) | Fremgangsmaate for fremstilling av 2-amino-5-hydroksy-4-metylpyrimidin-derivater | |
| CA1156655A (en) | 2-amino-3-[hydroxy(phenyl)methyl] phenylacetic acids, esters and amides | |
| US4503073A (en) | 2-Amino-3-(alkylthiobenzoyl)-phenylacetic acids | |
| EP3544965A1 (en) | Sulfoximine, sulfonimidamide, sulfondiimine and diimidosulfonamide compounds as inhibitors of indoleamine 2, 3-dioxygenase | |
| US7132541B2 (en) | Crystalline fluoroquinolone arginine salt form | |
| CA1128512A (en) | 2-amino-3-benzoyl-phenylacetamides and cyclic homologues | |
| DK160486B (da) | N-(4-amino-2,2-diphenyl-butyl)- eller n-(3-amino-2,2-diphenyl-propyl) urinstofforbindelser, fremgangsmaade til fremstilling af disse, samt en farmaceutisk komposition | |
| EP0134928A1 (en) | Imidazo[1,5-a]pyrimidine derivatives and process for their preparation | |
| US4333951A (en) | 2-Amino-6-biphenylacetic acids | |
| EP0089426B1 (en) | 2-amino-6-biphenylacetic acids | |
| CA1147746A (en) | 2-amino-3-(alkylthiobenzoyl)phenylacetic acids | |
| GB2068963A (en) | Basic ethers of 4-hydroxy-benzophenones acting as beta-blocking agents and relevant preparation processes | |
| US4251541A (en) | 1-Substituted-3-arylthio-4-hydroxypyrrolidines | |
| US3821415A (en) | Heterocyclic compounds in pharmaceutical compositions and methods | |
| US4051259A (en) | Phenoxyacetic acid amide | |
| DK142844B (da) | Analogifremgangsmåde til fremstilling af substituerede N-(2-pyrrolidylmethyl)-benzamidderivater. | |
| US3668205A (en) | Benzylamino quinazolinyl formamidine compounds | |
| CA2369654A1 (en) | N-substituted-n'-substituted urea derivatives and pharmaceutical compositions containing said derivatives | |
| CN108586341A (zh) | 酰胺类化合物和其药用盐及其制备方法和药物用途 | |
| CA2459407A1 (en) | Crystalline fluoroquinolone arginine salt form | |
| JPH0798824B2 (ja) | 免疫調節剤 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |